The Trouble With Love
by AngelVanguard
Summary: Dean Winchester used to date Brooke Davis, but they had a falling out. Dean moved on and started dating Cassie, but has he really moved on when he can't get Brooke out of his mind.
1. Wish I Could Forget

Cassie looked at Dean and asked, "So what do you want to do tonight?"

Dean glanced at Cassie, but he didn't see Cassie. Instead he saw his ex girlfriend, Brooke Davis. Dean did not know why, but lately all he could think about was Brooke. It had been six months since they last saw one another, yet just two months ago is when he started seeing Cassie.

Dean and Sam had been working a case, and she just seemed to be everywhere he was. Of course she doesn't know what his occupation is; she just thinks he is connected with the law somehow and is undercover. Dean didn't know why he stayed with Cassie and started seeing her to begin with. Maybe he was just drawn to her, or maybe the real fact was he thought he could get over Brooke faster by dating someone new.

Now it's been two months that they have been together and all he can do is think of Brooke. I guess that just proves that dating someone new can't make you forget the past; which is exactly what Sam had told him. Dean still refuses to believe that he is just too stubborn to listen to reason.

Cassie noticed how it was like Dean was not even there at all. Cassie waved her hand in front of Dean's face. Dean looked at Cassie she stated, "Hello earth to Dean."

Dean spoke, "Yeah what's up?"

Cassie questioned, "I was just wondering what you wanted to do tonight?"

Dean answered, "Whatever you want babe."

Cassie said, "Well I was thinking of making reservations at the Blue Skies."

Dean kissed Cassie on the cheek and replied, "Whatever you want babe. I just got to go make a quick phone call." Cassie nodded as Dean left the house to go outside.

Dean walked across the street and went over to his car. Dean leaned against the hood of his Impala and pulled out his cell. He scrolled down his address book until he came across the name Brooke Davis. His finger grazed over the talk button; he contemplated calling her or just leaving it alone. Then when he went to shut his phone he accidentally hit talk. He just stared at the phone for 15 seconds until he put the phone up to his ear and waited.

On the other end Brooke was driving home from a game when her cell rang. She looked at the caller ID, and it read Dean Winchester. Brooke didn't know what to do she has not heard from Dean in six months. Brooke instantly _thought something was wrong why else would he be calling_. Brooke hit talk and spoke, "Hello."

Dean closed his eyes and thought _god it feels so good to hear her voice._ Dean said, "Hi, Brooke."

Brooke's heart stopped when he said her name _she could not do this._ Brooke could not do the small talk right now, so she asked, "What do you want Dean?"

Dean felt his heart tearing in two after hearing the tone in her voice. Dean swallowed back his feelings though and said, "I just wanted to talk."

Brooke puzzled, "About what? What could you possibly have to say to me?"

Dean answered, "I want us to be friends I need you in my life Brooke." Brooke's heart instantly stopped and she was speechless, but that was about to change. "As a friend I mean I miss your friendship."

That right there did it for Brooke she was plenty steaming now, "Oh I see…" Brooke stated, "So you missed my friendship the past six month, but not the relationship right?"

Dean felt tears building up in his eyes and he held them back, "Brooke it's not like that."

Brooke exclaimed, "It's not? Are you sure about that, because that is what it sounds like to me? God you call here after six months of just ending things out of the blue, and you expect me to just be your friend."

Dean felt a few tears slip down his cheek he responded, "Brooke, I regret how things ended between us." Brooke felt tears sliding down her cheeks as well "But, I don't regret us ending. It was just…it was time for us. I miss you being in my life and I don't want you completely out of it."

Brooke began crying as did Dean and they could both hear one another's voice cracking; which was killing the both of them. "I'm sorry Dean I can't be that for you" Brooke then hanged up and really started crying.

Dean heard the dial tone and then closed his phone. Dean wiped away the tears and regained composure; once he was sure he looked fine he headed back into the house.


	2. Something Or Someone Is On Your Mind

A week goes by and Cassie can sense something is wrong with Dean she just can't quite place it. Dean comes to Cassie's house to pick her up for dinner. Dean notices Cassie is not dressed for dinner he said, "Come on woman get dressed." Cassie looked away and Dean knew something was wrong "What's up?"

Cassie spoke, "We need to talk" Dean nodded at her. "Listen Dean, I know something is wrong with you, and I want you just to be completely open with me."

Dean thought of back when Brooke had this same conversation with him. Although it was about his job not because of something or more someone else. Although of course, Cassie does not know there is a someone else he is thinking about.

"Dean, Dean, Dean!" Dean snapped back to reality to see a frustrated Cassie. "See this is what I am talking about" Dean gave her _what_ look. "You just zone out on me all the time." Dean remained silent "Don't you have anything to say?" Dean shrugged and still says nothing Cassie exclaims, "Fine I don't feel like going out now." Dean nodded and turned and exited the house. Cassie sighed just watching him not even second glancing and leave.

Meanwhile in Tree Hill during a basketball game Peyton had noticed all week that something was up with Brooke. Peyton questioned, "Alright B. Davis what is up?"

Brooke puzzled, "What do you mean?"

Peyton responded, "You have not been yourself all week."

Brooke replied, "I got a call from Dean."

Peyton's eyes grew wide and asked, "What did he say?"

Brooke said, "He wants to be my friend."

Peyton puzzled, "And what did you say?"

Brooke questioned, "What do you think I said?" Brooke gave her a _duh_ look.

Peyton stated, "Maybe it would not be the worst thing Brooke." Brooke looked at her best friend. "Just a thought I mean you gave Lucas and I lots of chances to redeem ourselves. Now here is Dean and he is just looking for a second chance." Brooke really did not say much after that because Peyton made semi sense.

After the game Peyton, Lucas, and Brooke were walking out towards the parking lot. Peyton asked, "Brooke, you need a ride home?"

Brooke went to answer until something caught her eye and she stopped mid track. Lucas spoke, "Well I don't believe it."

Brooke glanced at Peyton who gave her a smile and motioned for her to go on. Brooke left Lucas and Peyton and said, "Hi, Dean."

Dean spoke, "Hi, Brooke."


	3. I Just Had To See You

Brooke looked surprised at Dean who was leaning against the hood of his car. Brooke asked, "So what brings you to Tree Hill?"

Dean shrugged and replied, "I don't know…I just hopped in my car to for a drive, and ended up here." Brooke nodded at him "Need a ride home?"

Brooke spoke; "Sure" So Dean drove Brooke home. Brooke opened her car door and prepared to exit "Thanks for the ride."

Dean said, "No problem."

Brooke questioned, "Well, are you coming in or what?" Dean smiled and the followed her inside.

About an hour later Brooke and Dean were hanging out in Brooke's kitchen. Brooke asked, "So how is Sammy?"

Dean answered, "Still geeks don't know if I will ever get him to be as cool as his big brother."

Brooke laughed slightly and the debated about breaking the sweet moment they were having. Brooke questioned, "So, Dean I was just…" Dean glanced up at her. "I just…why after all these months did you decide to call out of the blue?" Dean cocked his head to the side and his expression soften "Why now?" Dean really didn't know how to answer her. "Because I have been trying for months to forget you and move on." Dean looked away from her "Than you call me and all those feelings come flooding back." Brooke's voice starts cracking Dean Looks up at her and he hates seeing her this way. "Dean…I…love you."

Dean looks at her blankly and tries to say something, but can't. He stated, "I can't get you out of my head, but Brooke…" Dean just looks at her and his eyes begin to glisten.

Brooke looked at Dean's changed expression and then it hit her. Brooke nodded and held back the tears that were stinging in her eyes. Brooke replied, "You're with someone" Dean looked away her "Why did you come back here Dean?"

Dean spoke, "I just had to see you." Dean connects eyes with and silence fills the air all Brooke does is nod at him.

The next morning Dean prepared to head back and he said, "I folded the blankets and left them on the couch."

Brooke nodded then gave him a hug as she watched him get into the Impala. Brooke stated, "Be safe." Dean smiled at her once more then drove away. Brooke watched until he disappeared completely out of her sight. Brooke's mind swept with thoughts _just like Dean to keep people at arm's length. Brooke knew though that when he does let you in it is pretty amazing what you find._


	4. Fixing It With A Lie

Dean went back to Cassie after leaving Tree Hill he sighed as he pulled up to her house. He could see her from the kitchen window she was baking…she always did that when she was upset. Dean got out of the car and headed to the door of the house and instead of just going right in like he usually did he stayed on the outside and knocked on the door.

Cassie glanced out the window after hearing the knock on the door and spotted the Impala. Cassie took a deep breath and went to the door she opened it giving Dean a stern look. She crossed her arms across her chest and Dean stated, "Alright I deserve that look."

Cassie asked, "What are you doing here Dean?"

Dean questioned, "Can I come in?"

Cassie puzzled, "Why?"

Dean licked his lips and replied, "Because I made a mistake I am not perfect and I am asking for your forgiveness."

Cassie's face slightly softens and questioned, "You're not perfect?"

Dean replied with a slight smirk, "Do I look it? I know looks can be deceiving."

A smirk finally appeared on her face she stepped away from the door and spoke, "Come on in."

Dean walked into the house and closed the door behind him; Dean puzzled, "So I am forgiven?"

Cassie responded, "Oh no you have a lot of making up to do."

Dean smiled and replied, "Oh yeah?" Dean picked her up and held her in his arms he climbed the stairs taking them into her bedroom, and carefully placing her on the bed.

Cassie remarked, "I said making up not making love."

Dean cocked his head to the side with an arched eyebrow and asked, "There's a difference?"

Cassie shook her head while laughing, "You just think you're so smooth."

Dean added, "And cute don't forget about that."

Cassie grabbed onto his shirt to pull him down to her and said, "Oh can't forget about that….so let's see this making up you have in mind."

Dean gave her his famous smirk, "Absolutely." Dean leans down to plant a kiss upon her lips.

A few hours later Dean and Cassie were lying in bed together after some heavy duty making up. Cassie had her head laid upon his chest and was wrapped up in his arms. Cassie said, "It really is great to have you back."

Dean remarked, "Oh are you saying you only missed me for my sex that I offer."

Cassie laughed, "Absolutely."

Dean expressed, "I am hurt."

Cassie replied, "Sure you are, but seriously glad you came back" Cassie paused for a moment and then asked, "Where did you go last night?"

Dean pressed his lips together and answered, "I needed some time to cool off, so I went to see a friend in the next town over."

Cassie questioned, "Oh in Tree Hill?"

Dean responded, "Yeah…" There was a lingering hint of question in his tone though by the way she asked him.

Cassie caught onto the tone and said, "I got offered a job there."

Dean looked down at her and puzzled, "When?"

Cassie answered, "Last night….to work at a magazine called Thud."

Dean slightly nodded and questioned, "Are you going to take it?"

Cassie spoke, "I don't know yet."

There was a long pause between them and before either one of them could speak up Dean's cell phone was ringing. Dean reached for it and picked it up without even looking at it…it had to be Sam anyways he always had impeccable timing when it came to him being in bed. Dean answered, "Hello."

"Okay so I have been thinking about it since you left and I think yeah okay….why not…we can be friends I mean I don't have to worry about my heart or that it will go beyond friends because you're with someone I mean…I am right…right?" Brooke just started rambling off without him getting an edge word end besides his first word…which she only did when she was really unsure of something.

Dean licked his lips he glanced down at Cassie giving her an uncomfortable smile. Dean didn't know what to say but, "Uh…huh…"

Brooke replied, "Uh…huh? That's all you have to say for…" Then it hit her and her voice trailed off. "Oh my goodness you're with her…"

Dean once again spoke, "Uh huh…"

Brooke asked, "And in bed?"

Dean still said, "Uh huh…"

Brooke nodded and laughed, "Okay…good…good for you I mean…you were always good in bed…I mean…yeah call me later." Brooke instantly hung up and hit herself for saying what she just did.

Dean was mortified not as he was sure Brooke was. As he shut the phone he made sure to turn it off completely and Cassie asked, "Who was that?"

Dean instantly spoke, "Sam….he realized I was…"

Cassie started busting up laughing, "In bed…" Dean nodded "Poor Sam."

Dean took a deep breath and said, "Yeah…poor Sam."

Cassie questioned, "So maybe we could go into Tree Hill and check out the town." Dean was completely not there as he was thinking about Brooke wanting to start a friendship and what started that. "Dean."

Dean looked down at her and questioned, "Yeah?"

Cassie puzzled, "Where did you just go?"

Dean answered, "Just thinking about What Sam's expression looks like right now" Dean tried to smile as he lied right through his teeth to her.

Cassie replied, "You're bad."

Dean takes a deep breath and releases, "Yeah I know." Dean is glad he shut off his phone don't need any more close calls.


	5. Are You In Or Out?

It had been at least a month since Dean had left Cassie…that was it they were over. Did he think about her yeah of course, but he had been in contact with Brooke and she occupied his mind more. Dean was asleep in the car as Sam was driving them down the road. Sam came to a stop and pulled up to a house and parked in front of it...

Sam said, "Dean wake up we're here."

Dean stirred and looked around and asked, "Where are we?" Dean then registered where they were "No scratch that…why the hell are we here."

Sam stated, "Because you are a love sick puppy and I'm sick of it."

Dean exhaled loudly, "Sammy."

"Oh good you're here and by the looks of Dean's expression he just found out that your plan" Peyton said.

Dean looked at Sam as he got out of the car and questioned, "What plan?"

Peyton arched an eyebrow at Sam as he got out of the car and replied, "Or he hasn't…sorry."

Sam stated, "This is operation Brooke and Dean reunited."

Dean replied, "She wants to be my friend and after everything I've done I am learning to deal with that. I don't want to screw this up further."

Peyton remarked, "You won't because you have me…an insider someone to tell you things and help you out when you're not there."

Sam stated, "Listen if you're really mad about this then we'll get the car and she'll never know you were here, but we can stay and get this right for you."

Dean cocked his head to the side and asked, "Yeah and when we fix this and it's time to go…what then…I will just break her heart again."

Peyton remarked, "We already got that figured out too." Peyton and Sam smiled at one another.

Dean puzzled, "And what pray tells is that?"

Sam answered, "You ask her to come with us."

Dean scoffed a laugh at that, "Yeah right I can so see that one happening."

Peyton gave Dean a sincere look and spoke, "She will…I know she will because before she said that if you would've asked her to go with you…she would leave everything behind and just go with you because of how much she loved you. Now are you willing to fight for that love again or are you going to keep living your life in regret?"

Dean looked shocked by Peyton's confession about Brooke and looked down to the ground as he ran his hand through his hair and looked at Peyton and Sam who were both here trying to do such a good thing. Dean took a deep breath and released it slowly and spoke, "Alright let's do this." Sam and Peyton smiled at one another and Dean hoped this wouldn't be the death of Brooke and him.


End file.
